In 2014 we appraise hip-hop on its forthrightness. Take, for example, the two front-runner Grammy-nominated hip-hop albums of 2013: Kendrick Lamar’s Good Kid M.A.A.D. City and Macklemore’s The Heist. Both albums, in different ways, present up-front opinions on the word we live in, be it the gangland problems still present in Compton or the bigotry persisting in American suburbia. Forthrightness is a valuable thing, especially in a world where mainstream and so-called underground hip-hop both resemble dance pop more and more with each passing month.

However, there’s something to be said for decoding. The hip-hop community has produced plenty of classic albums with somewhat obscure lyrics — lyrics that that require multiple listens to untangle and unpack — from Wu Tang Clan’s Enter The 36 Chambers, to the Beastie Boys’ Paul’s Boutique, to pretty much everything Kool Keith ever recorded. These albums require time and attention. Theoretically, hip-hop lovers grew close to those artists by poring over their wordplay and deciphering the meanings therein. And in the aughts, at least, no emcee did obscurity better than Aesop Rock.

Born Ian Bavitz, the Brookyln-bred emcee played an important role in the proliferation of underground hip-hop at the turn of the century. His albums with NYC’s Def Jux records are among the best work that the backpack-rap scene produced. That movement was curated largely by Slug, of Minneapolis duo Atmosphere, and El-P, cofounder of Def Jux. But both of those emcees dwelled largely in their own worldviews and personas. Aesop looked at the world around him and spent much of his career relating what he saw — and what he saw looked both whimsical and bleak.

Figuring out what he had to say, however, remains a task. Aesop still spits by Emily Dickinson’s mandate to “tell all the truth, but tell it slant.” His flow feels like water gushing from the crack in a dam. His verses are often endless streams of ten-dollar words, rife with double entendres and esoteric cultural references — this is a man who will drop allusions to Lord Of The Rings, Issac Asimov, Marx, and Dostoevsky in a single record, with no regard as to whether his audience knows what he’s talking about. His clever wordplay sometimes comes at the expense of the beat, as he often runs over a bar and halfway into the next before finishing a couplet. Call him the patron saint of the enjambed line. At maximum capacity, an Aesop Rock song sounds like the stylized ravings of a man tumbling down a hill, filling the air with thoughts in the moments between his face hitting the dirt.

Which isn’t to say Bavitz is all style and no substance, as his critics frequently claimed. The tattoos on his forearms read “Must not sleep/ Must warn others,” a mandate to educate his audience on injustice, as well as a reference to Invasion Of The Body Snatchers (Aes quotes this exact line on his off-album track “Dust Storm,” a must-listen). His lyrics often meditate on city life, economics, ethics and other important-but-human topics. Bavitz is simply unafraid of twisting his subjects around themselves until they become Gordian Knots — in fact, he seems incapable of expressing himself any other way.

If he’d delivered an album like 2001’s seminal Labor Days with Macklemore’s congeniality, people might not have stood for it. Bavitz was Caucasian, raised Catholic, and attended a top-tier public high school at a time when those were still unusual traits in commercial hip-hop, at least on the surface. It was his oddness, however, that made him a breath of fresh air. Where even progressive emcees like Nas were interested in race politics, Aes was more concerned with growing class disparity. While his contemporaries were concerned with accumulating money, Aes wondered why there wasn’t enough for everybody — or why money even matters. His stories are mostly nonviolent, he mourned the sorrow of others rather than celebrate his victories, and he seemed utterly disinterested in flaunting sexual escapades or substance abuse. Even in the company of Def Jux emcees, that was unusual. That kind of originality is exactly why Aesop Rock deserves to be remembered and celebrated right now. So here we are, counting down all of Aes’ major work, LPs and EPs (leaving aside the blatantly inessential stuff like the jogging soundtrack he made for Nike), from worst to best.